Many bacteria that are pathogenic to man possess menaquinone (Vitamin K2) in their electron transport chain. This menaquinone they manufacture internally using the "shikimate plus glutamate" biosynthetic pathway to construct the 1,4-naphthoquinonoid ring system. The details of this pathway are not yet certain. The proposal seeks to remedy this situation. The pathway will be examined first in root cultures of Impatiens balsamina--a system that forms the simple material 2-hydroxy- 1,4-naphthoquinone. The results will then be checked in the menaquinone-producing organisms, M. phlei, C. diphtheriae, B. megaterium, and S. albus. A combined computerized mass spectrometer/radio gas chromatograph will be used in the work. When details of the biosynthetic route are forthcoming, structural analogs of intermediates in it will be prepared and tested for inhibitory action on menaquinone synthesis. It is hoped to develop broad spectrum antibacteria drugs by this means.